


The First Time Isn’t Always The Worst But It Certainly Is Awkward… For Some…

by DeathsLastPrayer



Series: A Series of Unrelated Events Starring Jean x Eren [6]
Category: Shingeki no Kyojin | Attack on Titan
Genre: Childhood Friends, Eren's First Time, M/M, Some Fluff, some porn
Language: English
Status: Completed
Published: 2015-06-14
Updated: 2015-06-14
Packaged: 2018-04-04 11:04:08
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 5,910
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4135116
Author URL: https://archiveofourown.org/users/DeathsLastPrayer/pseuds/DeathsLastPrayer
Summary: <blockquote class="userstuff">
              <p>In Which: Eren wants to lose his virginity to someone that he trusts so he picks Jean because they're childhood friends and he trusts him. Or, the one where Jean thoroughly enjoys popping Eren's cherry.</p>
            </blockquote>





	The First Time Isn’t Always The Worst But It Certainly Is Awkward… For Some…

##### 

* * *

I. 

* * *

Trust. 

That’s the key thing when it comes down to it. 

Trust… 

Not love or companionship or promises of forever or morals or values or religion or society or hearsay from friends/peers/media/parents. 

Just trust. 

Eren knows this –has had the lesson pounded into him since he was old enough to know what thought was and is. The concept has evolved with time but there are some key qualities tied into it along the way. 

First: Trust thyself. His mother used to tell him that it’s impossible to trust anyone else if he can’t trust in himself and his beliefs. Which is far easier said than executed, Eren knows this personally. He’s human so there are times when he’s not entirely positive about his ideas or actions or convictions but he tries to hold onto that trust in himself because it’s the foundation of, well… everything. Besides, his mother used to also tell him that, if he can’t trust himself, neither can anyone else trust in him so there’s that. 

So after somewhat cementing his trust in himself, there came an evolution: trust in others. But- See, not everyone deserves to be trusted and that’s where Eren thinks trusting himself really comes into play. He trusts his gut and his own judgment –can weed out those who deserve his respect and those who don’t. It’s as simple as that (but not really because, again, he’s human so he’s not without his flaws and mistakes). 

Finally: gaining the trust of others. Now, he’s figured out that that particular brand of trust is tricky because it involves too many components that are outside of him (like those first two renditions of trust that the other person needs to deal with). But it’s not impossible to grasp at and it’s an honor when it’s obtained so… he supposes it’s worth the effort to get another person’s trust because the reward is very humbling. 

But those are three main types of trust that are key when it comes to one thing in particular: having sex for the first time. 

Which is exactly why Eren knows who he wants to do this with and why. 

Now… getting that person to go along with things… well… 

Eren trusts his gut so there’s nothing more to it than that. 

* * *

* * *

* * *

“Wait, wait, wait… you want what?” 

“I want you to have sex with me, horse face.” 

Jean doesn’t know if he should be frowning or smirking or what but he blames this entire situation on Eren for always effectively catching him way the fuck off guard. “Who asks shit like that?” 

Eren shrugs, “I figured it was pretty straightforward and adult-” 

Jean snorts, “Adult would be not calling the guy you’re asking the favor of names.” 

“It’s not even an insult by this point,” Because Eren’s been calling Jean that name since they were gap toothed tots so it’s long since lost its bite. “But stop stalling. Yes or no?” 

“If I say ‘no’?” Not that he’s thought too much into that option this far into the conversation but, still… 

A dark brow raises, “I’ll ask someone else, so no pressure.” Although, Eren only has three other options and if they all say no then he’ll have to wait… and he doesn’t exactly want to do that but he can and will if he has to. On the other hand, he trusts Jean more than anyone else, at least when it comes to this so- 

“And if I say ‘yes’?” 

Eren rolls his eyes at that. “Then, naturally, we’ll have sex.” 

“How do you know I’d even consider having sex with a guy?” 

Okay. Maybe Eren didn’t consider that. He’s always known that he likes males –that a male partner is what he finds attractive and what he wants when it comes time to settle down but Jean… They’re 18 and Jean has been his neighbor since before they could even babble coherently. And Eren knows Jean well –too well for his liking but it comes with the whole being childhood friends. Even though they don’t hang in the same circles (not since junior high) or around each other as much as they did when they were brats, Eren would like to think that he still knows Jean –still can trust him and has Jean’s trust in return. 

It’s not like they’re strangers or anything just because they don’t hangout 24/7. 

Jean still comes in without knocking when he needs to borrow anything. Eren loves helping Jean’s mom in her garden and sitting in the back for tea and cake when they’re done. Jean still calls Eren’s mom ‘mum’ whenever he sees her and when soccer season hits, Jean and Eren’s dad root for the same team so they always team up against Jean’s dad. And Jean’s dad can always rope Eren into rooting for his team (even though Eren doesn’t give a shit) and Eren will and it’s an enjoyable couple of weekends when the games come on. 

So they’re still acquainted and- yeah. 

Eren didn’t consider the fact that Jean will say no because of his gender preferences. But he didn’t think he needed to consider that because he didn’t and doesn’t think it matters when it comes to them. And, if it does- “Would you? Consider it I mean?” 

Jean frowns and stares and then- “It’s you who’s asking so- fuck… fine. I’ll pop your fucking cherry but we’re doing it my way. God… who even waits this long to do shit like this.” It’s a rhetorical question but still. 

“Thanks.” Eren smiles because he did factor in the fact that Jean has never actually told him ‘no’. He’ll grumble and complain and they’ll argue until their throats are raw or they’ll brawl but Jean always ends up doing what Eren wants in the end. It’s been that way since they were brats. But Jean also tries to compensate for giving in by saying ‘we’ll do it my way’ and Eren doesn’t mind giving him that much leeway. 

“My folks are still going out of town this weekend so I’ve got the house to myself. I have practice on Friday and this bonfire and then a game on Sunday so… Saturday.” He can skip the party on Saturday –it’s nothing demanding or anything. Plus, it’s not too often that Eren asks him for anything these days (odd as this particular request may be) but- Honey colored eyes meet blue-green and Jean frowns, “Don’t you want to do this with, I dunno, someone you love or some shit?” Isn’t that what everyone strives for, at least for the first time? 

Eren shakes his head, “That’s where everyone goes wrong the first time. I’d rather do this with someone I trust as opposed to someone I’m with in the _right now_ and it’s a fleeting whim and it’s all shitty, yeah. I mean, at least if it’s you and you suck I won’t feel bad telling you that much and you’ve seen me at my most embarrassed and you’ve seen me when I’ve fucked up so, really, I’m not trying to impress you or anything. I can just be myself and I would prefer that for the first time.” 

Jean runs a hand through his hair and sighs because- seriously. Only Eren… 

“Was your first time with someone you loved?” Eren knows that Jean dates a lot and he’s a popular guy at their high school so it’s not like he can’t but he also knows that Jean is a real sap on the inside so- 

“Yes, er- I thought I loved her. Summer before sophomore year when I was dating Hitch and it was our six month anniversary… It was awkward as all hell because neither of us had ever done it before and the after… let’s just say I got really good at fucking that summer.” But the first time was nerve wracking and kind of shitty, so Jean can’t blame Eren for having those expectations. 

“Good, you’ll know what you’re doing and I really won’t have to give a fuck about impressing you but now I have expectations so you better live up to them.” Eren laughs at the expression on Jean’s face when he pushes away from the kitchen counter. “I’ll see you. I gotta head to Armin’s but, text me or something if you change your mind, yeah. No hard feelings.” 

Jean bristles because he’s always hated how mature Eren is –how he’s leagues above the rest of them when it comes to these things. But, on Saturday… “I’m not backing out.” Saturday, he’ll shatter that entire persona. 

“Good. Don’t forget to do your research. I’m not a girl so it’s not the same.” And Eren leaves him with that lingering thought just before he shuts the backdoor. 

##### 

* * *

II. 

* * *

The week flies by in a flash but it isn’t until Friday night when Eren hears from Jean again and in the form of a text. He’s expecting cold feet but, instead, he gets: _you’re bottoming, right? I mean… umm… we can talk about it or something._

Eren laughs at that and waits about an hour to respond just to make Jean squirm and piss him off: _I’ll bottom. I’m the one losing my virginity, not the other way around, horse face._

Jean’s response is instantaneous: _Thank god! Not gonna lie, I was hoping you’d say that._

**_Eren:_** _Hmm… you been doin’ research?_

**_Jean:_** _Yeah, yeah. I got this. I got this._

**_Eren:_** _Well, even if you suck, just remember that I trust you enough to tell you._

**_Jean:_** _I’ll suck alright, but the only thing you’ll be saying is “more” ;P_

Eren flushes and stares at the screen and then he laughs a bit. Nervous laughter because he is nervous, even if it is just Jean he’s doing this with. And Jean is so sexually aware and relatively open all things consider so he didn’t make the wrong choice. He knows that. And it’s a good thing. 

So it’s not hard for him to text back, _I’ll hold you to that._ And then he shuts off his phone and gets ready for bed because tomorrow is kind of a big day but not really at the same time. 

* * *

* * *

* * *

He wakes up to his door being knocked open and Jean plopping down on his bed and rustling his hair and it’s so goddamn annoying- “Get the hell off…” He mumbles and pushes feebly at Jean’s side. 

Jean just grins, “Get up. We’re going to the mall. Wear something decent.” And then he’s out of the room. 

Eren groans and sits up and wishes he could have slept until four because it’s Saturday and he deserves that much after gaming with Armin and Reiner until 6AM but whatever. Jean’s terms… right. So he drags himself out of bed and makes it down the hall to the shower, which wakes him up in an instant. Reminds him that it’s _that_ Saturday and he has to take a slightly different sort of shower. The kind where he’s squeaky clean –inside and out. And Eren goes through the motions because he’s practiced a bit himself (because it’s something he wants to do so why not). 

It takes all of 45 minutes to shower and get dressed and when he walks into the kitchen to kiss his mom, he assumes he’s dressed nice enough because Jean eyes him and his gaze flashes and Eren feels a bit undressed under that gaze but tries to ignore it. 

“I hear you’re helping Jean house sit tonight. No parties, you two.” 

Jean laughs and hugs her easily enough, “You’ve got nothing to worry about, mum. Eren never lets me get away with anything.” 

“Damn straight! No parties, promise.” Eren gives his mother a quick kiss to the cheek before tugging at Jean’s collar “I’ll call you later.” He waits for Jean to get in before asking, “What’s your plan, since we’re doing this _your way_?” 

Jean grins and starts the engine, “We’re going shopping cuz I need a few things, then a movie, we’ll nab something to eat, and head back to my place.” 

That sounds suspiciously like, “A date?” 

Jean shrugs. “Yes and no. I figured, I respect you enough to at least take you out before we pop your cherry. I mean, that shit’s special to most people but you’re weird as all hell like always so… let’s call it celebrating the start of your sex life.” 

Oddly enough, Eren likes the sound of that. “Alright then, lead the way.” 

* * *

* * *

* * *

The Mall: Eren wanders into H &M because it’s cheap and he loves their skinny jeans and he tries on a pair of ash gray ones that Jean likes when he sticks his head into the dressing room (says they make Eren’s ass look incredible –objectively of course). So Eren buys them because he happens to like them too (gets ‘em in black, maroon, and charcoal) and then he gets a few shirts and some suspenders. (That sparks up some bickering because Jean wants to know “who the fuck wears suspenders” and Eren wants to know “who the hell wouldn’t” but then he puts them on with his jeans and white V-neck that hugs him just so and- yeah, Jean approves). 

Jean stops to get new cleats and then drags Eren to the music store for headphones and records (because Eren swears that Jean’s secretly a hipster) but it’s fun because they listen to music and remember that they’re kind of in to the same artists so there’s that. 

Eren can’t resist the arcade so he makes Jean go in and put a 20 in the quarter machine and they waste it all on Time Crisis 4 but have no regrets because Eren kicks Jean’s ass where points are concerned but they beat the game and the shit talk keeps things interesting –the shit talking and bets that make Eren flush to his toes but he pulls off not letting Jean in on that. (Like when Jean says, “Bet you a blowjob I score higher than you this round” and Eren says, “Deal” and then he wins and wonders if he really won a blowjob or if they’re just being teenaged pricks but supposes he’ll find out later). 

That’s the mall. 

The Movies: Jean’s pays for the tickets because it was his idea to go and Eren tells him it’s only fair considering he picked the movie (not like Eren didn’t want to see it but still). They don’t get anything more than candy because they still want to go eat after –need a nice appetite, no need to ruin it. They go see the new Insidious movie and it’s scary as all hell –makes Jean wrap his arm around Eren’s shoulders and pull him close and bury his head in Eren’s neck (and if he lingers because Eren smells nice or is warm, no one has to know). Eren thinks Jean’s reactions are funny and ruffles that soft hair and holds the big baby’s hand when he’s not being squeezed to death. Eren’s always been a horror fan so it’s nothing to him. 

And then they go out to Eat: Nothing too fancy, just a Thai place where Eren gets spring rolls and veggie fried rice because he’s thinking about what they’re going to do later and he can’t afford to eat too much or what he really wants to eat until later. Jean doesn’t get it and tells him to eat until Eren explains and then he’s blushing and getting shit for later –for after. The gesture makes Eren smile to himself but he changes the subject. 

They talk about Jean’s life as the star soccer captain and popular king and how that sort of spotlight is a bit ironic when he hates attention and people but he handles it well all the same. They talk about Eren’s studies and how he’s secretly just as popular in his own right because he’s charismatic as all fuck (Jean’s words) but he’s also so fucking aloof (Jean’s observations)… whatever. The conversation is nice and flirtatious and hostile at some points (when Eren says sports don’t compare to studying, Jean takes offense but not nearly as much as Eren does when he calls psychology a “fake science”) and hilarious at others (like when they reminisce about their childhood and the shit they used to get into). So it’s an entertaining dinner that never dulls. 

Reminds Eren that they’re still pretty good friends even if they don’t hangout all of the time or float in the same social circles. They’ve got a history that no one can erase or replace so whether they hangout now or a decade later, they’ll still be good friends. 

After Dinner: Eren chalks it up as a stellar celebration and when he gets in the car, he lets Jean turn on the radio because it drowns out his nerves and anticipation and- yup. He doesn’t mind. 

But he doesn’t know that Jean’s just as nervous and anticipatory as he is. 

##### 

* * *

III. 

* * *

Jean’s room. 

Eren’s been in Jean’s room over a thousand times throughout his life but this time… this time seems different. Very different. 

Like how he gets there for starters. 

With Jean coming up behind him after he shuts the front door and bracing strong hands on a trim waist and pressing cool lips to the base of Eren’s neck before saying, “Don’t worry, I’ve got this.” It’s Jean’s signature saying whenever Eren’s needed reassurance. Yet, it sounds different because Jean’s voice drops and is husky and Eren’s never heard him sound like that. 

But Eren nods and arches his neck and lets Jean’s lips move –shudders when that hot mouth opens and Jean’s tongue and teeth connect with skin. Tug and pull and tease. Wring a needy mewl from Eren that stirs the blood. 

Makes Jean chuckle against his throat as he steers him towards the stairs with hands untucking Eren’s shirt and unclasping those suspenders… 

Eren’s not really sure how they make it to the room because he gets pinned to the steps and spun around and then there’s Jean’s mouth on his and Eren’s not new to kissing –far from it. He pegs himself a damn good kisser but Jean… Jean’s mouth is an unearthly thing. Makes him chase after it and crave for it because he loves when Jean tips his head and slicks their tongues –plays a game of tug-o-war and wins and caresses gums and cheeks and- and Eren’s mind falters for a bit but he blames lack of air. So he’s not sure how they make it to Jean’s room when they stop every so often to devour each other’s mouths and pull at shirts and pants. 

And then he’s on the bed and Jean goes to follow but knocks his head on the wall, which makes Eren laugh and Jean scowl, “Ah, shit…” Jean sits up and stares, face twisted and hand rubbing at his forehead. 

Eren smiles, “You alright?” He sits up on his elbows, blue-green eyes constricted because he’s still horny, despite the slight disruption. 

“I’m good but how fucking uncool.” Even though he says that, Jean manages a grin and takes a second to tug his shirt off. 

And Eren really, really likes Jean’s body type –fit but not too much so and with enough definition to define that he’s active. Very nice. “I told you, you don’t have to try to impress me –not really. I know you. Your good and your shitty sides.” 

Jean hums and grips the waistband of Eren’s pants, “Well, if I suck at blowing you, just remember I’ve never done this shit before so don’t expect much.” 

Eren shrugs, “I’m not bad at it so I’ll give you some pointers if it’s god awful.” 

Jean pauses and stares –gaze trailing from Eren’s gorgeous teal eyes to his swollen lips. Fuck if the image doesn’t bring him to full mass –makes him hard as a fucking rock just imagining Eren between his legs and- “I learn better seeing shit happen as opposed to being told how.” 

That makes Eren chuckle all sinewy and he sits up and slides to the edge of the bed where Jean’s standing between his legs and Jean’s crotch is chin level… “I’ll give you one free lesson but, after that, you owe me.” 

Eren takes his time tugging at Jean’s already sagging pants and grasping the top of his boxers before pulling them down and making Jean hiss the instant his cock meets the air. And Eren stares because Jean is very nicely sized but he vaguely remembers that always being the case… That said, he holds onto Jean’s sturdy hips and wets his mouth –leans forward, lips wrapping around the head and tongue licking up the slit as he stares from beneath heavy lids and meets Jean’s gaze just as he pulls away to nudge Jean back. Eren doesn’t mind kneeling on the floor because it’s easier that way. 

More so when he gets Jean to lean against the wall by the window because then he has the chance to trail his tongue down the shaft and to the balls where he can mouth them and hum and he doesn’t flinch when Jean grips his hair. 

“Fuck…” 

And Eren enjoys deep throating –enjoys kissing the tip just before pushing it past his lips and letting that strong girth slide down his throat where he hums and moves his tongue along a thick vein as he bobs. Where he cups the balls with one hand and works the other up and down –from base to the space where his mouth can’t quite reach. Eren loves it. Giving head. 

But he’s always liked the reaction he draws out from giving far more. 

See, Jean grips his hair and mutters cusses and holds him in place and makes him gag a bit but that’s all part of it so Eren doesn’t mind. He even likes hearing his name fall from Jean’s mouth because it sounds guttural and like he’s being prayed to and a little hubris goes a long way. 

“Fuck, fuck… gonna- fuck, Ere! Stop before I- gonna cum…” 

Eren stops. Leans away and stares and Jean’s dick is hard and slick with precum and spit. Looks so ready- makes Eren hot and he’s already fidgeting because sucking someone off gets him off too so his jeans are torture and staring at Jean has every inch of him blazing. Unbearably hot. 

It’s almost like Jean can read his mind because, next thing he knows, Jean’s kicking out of his pants and pulling him up and kissing him like he’s the only source of air in the entire room. It makes Eren melt. Makes him ridiculously delirious with want because Jean’s tasting himself and not giving a fuck and picking him up just before crashing him into the bed. 

Reminds Eren that Jean’s good with his mouth too but for different reasons. 

Jean can plunder and pillage his mouth but then he drags it to his jaw, draws a line of butterfly kisses to his throat before sucking at a bobbing Adam’s apple. He takes his time at the neck –nips with his teeth and massages with his lips and burns with his tongue, yet, he still manages to electrify the skin and make Eren quiver and arch and draw out his name. He gives the same attention to Eren’s clavicle –leaves a gorgeous reddening splotch right where the collar meets the sternum. And he’s so very attentive. Especially when he gets to the nipples. Let’s his tongue roll the nub back and forth when it swells and pinches the other just so… Eren didn’t even know that his nipples were sensitive. 

But Jean seems good at this, at playing his body like an instrument he’s nurtured his entire life. 

When he pulls at Eren’s pants –kisses his way down the torso, mouths the bellybutton, and licks just above where those jeans are still buttoned- Eren sits up and catches Jean’s face between his hands because- “Not right now- returning the favor I mean. I mean, you’re good, yeah, but we don’t need to kill it with a first time blowjob.” 

Jean frowns a bit and it probably has to do with ego. Okay, a lot to do with ego knowing Jean. 

But Eren’s next words- “I really just want you in me and then we can test shit and have fun and be as sucky as we want to be while trying new things. But, first,” Eren draws Jean to him, their forehead knocking together harder than intended but it’s okay. “I want you to fuck me, Jean.” Realistically, Eren’s positive it’ll hurt the first time for sure. He’s practiced a bit with his fingers and he’s tried a dildo (which he couldn’t even get half-way in) so… so, yeah. It’s going to hurt a shit ton. 

But it might end up feeling good. 

And there’s the whole bit about trusting Jean –believing that Jean can make this half-decent. 

“Deal.” Jean goes a little flaccid when he gets rejected from giving Eren head but then Eren goes and tells him to fuck him with that canted mouth and those crazy beautiful eyes pinning him to the spot and Jean swears he could’ve cum then and there. “I did my research and I think I’ve got this.” He tugs Eren’s pants off –enjoys the flush of Eren’s cheeks when he’s all naked and exposed on the bed because he’s choosing now to be modest. 

Such a fucking turn-on. 

Eren laughs a bit. Nerves. “You have a big dick so don’t break me.” 

Jean snorts at that, “Thanks, but if I break you, it won’t be because my cock’s too big for your body.” He winks and moves towards the drawer to grab the condoms and the lube. 

He lets himself get a good look at Eren –at a side of his childhood friend that he’s never gotten the chance to see before. And Eren’s a beautiful guy –slender with fair skin and bright eyes and tussled hair. Looks better with the hickies because Jean has a thing for leaving his mark on the people he’s with. A reminder. But Eren shouldn’t taste so fucking good… seriously makes his taste buds tingle and thrive. And even seeing his dick isn’t a put off (and Jean was kind of worried about that killing the mood a bit but it doesn’t). See, that lets Jean know that he’s doing something right. That he’s the reason Eren’s hard and wants and craves. 

So he’s never seen Eren as beautiful and he’s never thought about wanting him or wanting to be buried in him but it’s not a bad thing. Because Jean does want. He wants to fuck Eren and mark him and make his first time memorable. 

Truth be told, Jean felt honored when Eren asked him. Taking someone’s virginity… no matter what Eren says, Jean thinks it’s something special and there has to be a trust there. Especially this –taking another guys virginity. Not because it’s weird or wrong or any of that but Jean’s never- not with another guy- so he can only imagine. Like, Eren’s trusting him with his pain and his pleasure and his mental state and a slew of other shit that’s so very different from doing it with a girl but then the same for some parts so- 

“I’ve got this.” 

Eren’s lips twitch into this soft expression, “I know. You never half-ass anything.” 

True enough. 

“It’ll be easier if I turn you around, just this time so you get used to everything.” 

“Alright.” Eren’s skin blossoms gorgeously but he does as Jean suggests. He gets on all fours and glances over his shoulder- “Like this?” He feels so ridiculous and vulnerable and- 

And then Jean’s moving. Pushing a pillow under Eren’s chest and telling him to, “Hold on to that and rest your head on the mattress.” Which Eren does and then Jean’s hitching his hips and spreading his knees and- holy mother. 

Eren feels open and they haven’t even gotten to that part yet. 

When Jean bites his hipbone, it startles him and he squirms and then he feels a cold, wet finger ghosting over his ass- 

“Need you to relax as much as possible, Ere,” Jean kisses Eren’s lower back and presses his finger against that tight ring of muscle- “Just relax,” He whispers in between kisses and he’s so surprised when Eren listens and his finger slides in and he pauses to let Eren adjust to the feeling but Eren just sighs… “You practice –doing this to yourself, I mean?” 

Eren’s so glad that Jean can’t see his face- “Ye- yeah.” 

“Fuck, Eren… that’s ridiculously fucking sexy.” Because it is and Jean can imagine Eren in his room all hunched over and fingering himself, mouth ajar and chin wet from drool… he wishes he could see him now. “I’m adding another and that’s when I’m gonna start moving ‘em.” 

“You don’t have to narrate.” 

Jean raises an eyebrow and wants to say something sarcastic and snarky but he’ll go with doing snarky and sarcastic shit instead, “Suit yourself.” 

Jean adds the second finger and Eren tenses up, grips those digits and makes Jean bodily shudder because he can picture himself in there and being gripped- He waits out a ten count before he starts scissoring his fingers and fucking Eren with that alone. And he’s getting off on watching those tan legs tremble as Eren rocks his hips ever so slightly but Jean’s looking for gold here. He read about it and if he does this right then Eren’s spot should be right around- 

“Ah… Jean!” Eren’s head snaps up and then slams into the mattress and he’s clenching so tight but, fuck. Fuck if he isn’t seeing stars and stripes and fireworks and feeling more pleasure than he conceivably thought was possible. 

Jean smirks. He found it so he lets his finger brush up against that gland and watches in fascination as Eren chases after the feeling by bucking just so and trying to reach it. Must feel incredible considering Eren barely registers when a third finger is added but, by that point, Jean can’t take it anymore. Can’t. Because he feels like he’s about to nut and he wants to fuck Eren until their legs give out. So he pulls his hand away (makes Eren whimper all sweetly) and stands up –almost trips over his feet because he’s that excited. 

Seriously excited if his hands are shaking as he rolls the condom on. 

When he climbs onto the bed, he presses his cock to the crack of Eren’s ass and leans forward, lips pressed to Eren’s shoulder, “I know you didn’t want a narration but, I’m gonna fuck you, Eren,” Jean smiles because Eren’s legs feel like they could give out at anytime and he’s achieving his goal –making the mature bastard fall apart at the seams. “Gonna make you cum and beg and call my name…” He sits up and takes hold of that trim waist with one hand, positions himself with the other- “We’ll take it slow but I’ll thoroughly pop your cherry.” 

Pushing in isn’t as easy as preparing Eren. 

Not even close. 

See, Eren tightens around the head and it’s painful as all hell so Jean has to tell him, “Relax. Come on… we’ve got this.” 

“Trying… fucking trying,” Is all that Eren gets out through gritted teeth. Because he is but it hurts and kind of feels like he’s being torn in two but he slips into his meditation mind and hums and bites down on the pillow as Jean slowly sinks in… 

“All in, Eren. Just, tell me when to move.” Jean waits and it feel like an eternity of being squeezed and tugged from Eren’s muscle contractions alone and it’s the most amazing feeling- 

Eren sighs and doesn’t bother to lift his head, just mumbles, “Okay.” 

Yes! Fuck yes! 

Jean starts slow and pivots and grunts and tries to cant his hips just so until he finds that spot- 

Eren’s breath pitches a few notches when he moans, “there! Right there!” 

And then Jean’s got it. Starts an awesome rhythm and bends to suck at a sweat damp shoulder blade as he snakes a hand beneath them to jerk Eren off to every well timed and well aimed thrust and- and fucking Eren is incredible. Being inside of him and listening to every moan or hearing his name roll off of that sweet tongue or even marking him… it’s driving Jean crazy and drawing him so close. 

“Jean…” Eren hates how his voice sounds but loves listening to the slap of flesh and Jean mumbling the dirtiest things into his ear. He wants to come and he wants Jean to make him do it and then he wants a break only to start again- 

“So close but wanna watch you. Want you to get there before I do- it’ll be fucking gorgeous.” Because it will be because Eren is and he can just make out the side of Eren’s face with that slack expression- 

And then Eren’s cumming into his hand and the walls of his ass are twitching and grabbing and gripping and bringing Jean to his own orgasm. Makes him buck and thrust with complete abandon that rattles the bed frame and leaves Eren gasping wonderfully. Makes him collapse on top of Eren once he reaches that point and he’s trying to catch his breath because- fuck. That was beyond amazing. 

Eren’s panting too and feels so alive and tired all at once- “You definitely don’t suck.” 

Jean’s laugh is airy and pairs with a kiss to Eren’s neck, “Good.” 

But here’s where the awkward is supposed to come into play and Jean’s kind of expecting it because, as mature as Eren is, they’re still brats and this is still Eren’s first time- 

“If you give me 20 minutes (because I want to eat something), think you can go again, this time facing each me.” Eren’s words are confident. 

Jean shouldn’t have expected anything less and thinks it’s pretty fucking awesome that Eren can pause for food and go again. Guys will love him. “Yeah. If we’re gonna do this whole popping the cherry thing, minds well do it thoroughly. But don’t get all awkward later and pretend that we didn’t do this.” Because Jean doesn’t think he’ll be forgetting anytime soon. And he can’t begin to comprehend what actually _seeing_ Eren fall apart will do to him. 

Eren laughs and twists his head to the side, “Don’t _you_ get all awkward and pretend nothing happened. I popped your man cherry so I say it’s an even trade.” 

Well… that’s equally true. Makes Jean smile because he hadn’t thought about that at all. And then he’s kissing Eren’s shoulder and definitely thinking about it and thinking about further popping both their cherries by turning Eren around and fucking him proper and then in the shower or the kitchen… 

“Won’t be awkward. I know your shitty side but I also know what you sound like when you cum so there’s that. Can’t get any closer or awkward, right.” 

“Yeah.” Eren nods and smiles to himself. 

He definitely didn’t make a mistake when he asked Jean. 

* * *

**FIN**

* * *

**Author's Note:**

> For anyone who's wondering (and since this was a one-shot): Eren and Jean shag the entire summer after senior year, go their separate ways for college, meet 6 years later when their parents have a New Year's thing, and end up together and spending the rest of their lives in lovers bliss. There you have it! 
> 
> Anyway, hope you enjoyed, thanks for reading, and if you dug it, don't be afraid to drop a line or hit that kudos button.


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